AI Native Rippling for Deskless Workers. Backed by Y Combinator.
About the role
The person who hears the customer, who takes the call when a scheduler can't get a guard clocked in, who sits with an operations manager during go-live, that person knows more about what we should build than anyone in a roadmap meeting. AI makes it possible for one person to hold both ends of that loop. So we're hiring for it as one role. You have real energy. You like a day that starts with a customer escalation and ends with a product spec. You move fast and you follow through.
What they're looking for
- Get deployed into our customers. Run implementations end to end: kickoff, data migration, configuration, training, go-live. A 300 guard company with 24 sites moving off ADP is a normal project here
- Pick up the phone. Schedulers, dispatchers, and guards call when something isn't working. Some of it is training, some of it is a real bug, and you'll know the difference fast
- Work directly with our CTO and engineering on what we build next. You'll bring the evidence, not opinions. What you heard, from who, how often, and what it's costing them
More about this role
The person who hears the customer, who takes the call when a scheduler can't get a guard clocked in, who sits with an operations manager during go-live, that person knows more about what we should build than anyone in a roadmap meeting. AI makes it possible for one person to hold both ends of that loop. So we're hiring for it as one role.
Sira is workforce management for deskless teams. Scheduling, timesheets, payroll, HR, compliance, and invoicing in one place. Our customers are security guard companies and commercial cleaning businesses running 50 to 300+ people in the field, and most of them are coming off a mess of ADP, Connecteam, spreadsheets, and paper.
We're YC S25, based in SF. Today 4,500 workers clock in on Sira. I was at Intuit before this working on QuickBooks Time and Payroll, so I know exactly how painful this software usually is. We're building the version that isn't.
I've taken every customer call myself since day one. Every implementation, every go-live, every 7am "the app won't let my guard clock in" call. It's the reason the product is good. It's also the reason I can't keep doing it alone.
We're adding customers faster than I can personally onboard them. So...
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